Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 15, Problem 30P
2,6-Dichlorophenol has been isolated from the females of two species of ticks (Amblyomma americanum and A. maculatum), where it apparently serves as a sex attractant. Each female tick yields about 5 ng of 2,6-dichlorophenol. Assume that you need larger quantities than this and outline a synthesis of 2,6-dichlorophenol from phenol. (Hint: When phenol is sulfonated at 100 °C, the product is chiefly p-hydroxybenzenesulfonic acid.)
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Benzoic acid, Ph-COOH (C6H5CO2H), is not soluble in water while it dissolves in ether (diethyl ether), (CH3CH2)2O. Yet upon treatment with sodium hydroxide, benzoic acid turns hydrophilic and dissolves in water.
Provide chemical explanation of this observation.
Eugenol is the component responsible for the odor of cloves, which are dried flower buds of the
evergreen tropical tree Eugenia aromatica. The isolation of eugenol from the rest of the constituents of
"oil of cloves" (comprising around 10% of acetyleugenol and caryophyllene) is highly dependent on the
chemically active proton of the phenolic group of eugenol. Draw the structure of the main components
of "oil of cloves" and describe how to isolate or extract eugenol considering its structure.
Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4.
The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - PRACTICE PROBLEM 15.1
Show how loss of a proton...Ch. 15 - Prob. 2PPCh. 15 - PRACTICE PROBLEM 15.3
Outline all steps in a...Ch. 15 - PRACTICE PROBLEM 15.4 Provide a mechanism that...Ch. 15 - Prob. 5PPCh. 15 - Prob. 6PPCh. 15 - Prob. 7PPCh. 15 - PRACTICE PROBLEM 15.8 Write resonance structures...Ch. 15 - PRACTICE PROBLEM 15.9
Provide a mechanism for the...Ch. 15 - PRACTICE PROBLEM 15.10 The trifluoromethyl group...
Ch. 15 - PRACTICE PROBLEM 15.11
Predict the major products...Ch. 15 - PRACTICE PROBLEM 15.12 Predict the major product...Ch. 15 - PRACTICE PROBLEM 15.13
Write mechanisms for the...Ch. 15 - Prob. 14PPCh. 15 - PRACTICE PROBLEM 15.15
Suppose you needed to...Ch. 15 - PRACTICE PROBLEM 15.16 1-Fluoro-2,4-dinitrobenzene...Ch. 15 - Prob. 17PPCh. 15 - PRACTICE PROBLEM 15.18
When...Ch. 15 - PRACTICE PROBLEM 15.19 Birch reduction of toluene...Ch. 15 - Prob. 20PCh. 15 - Prob. 21PCh. 15 - What monobromination product (or products) would...Ch. 15 - 15.23 Predict the major products of the following...Ch. 15 - Prob. 24PCh. 15 - 15.25 Starting with styrene, outline a synthesis...Ch. 15 - Prob. 26PCh. 15 - 15.27 Starting with aniline, outline a synthesis...Ch. 15 - Prob. 28PCh. 15 - Propose structures for compounds GI:Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - Prob. 31PCh. 15 - 15.32 Give structures (including stereochemistry...Ch. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 35PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 37PCh. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Prob. 40PCh. 15 - Predict the product of the following reaction.Ch. 15 - 15.42 When m-chlorotoluene is treated with sodium...Ch. 15 - Prob. 43PCh. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Prob. 46PCh. 15 - 15.47 Provide structures for compounds A and B:
Ch. 15 - Prob. 48PCh. 15 - 15.49 Treating cyclohexene with acetyl chloride...Ch. 15 - 15.50 The tert-butyl group can be used as a...Ch. 15 - 15.51 When toluene is sulfonated (concentrated )...Ch. 15 - Prob. 52PCh. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - A C-D bond is harder to break than a C-H bond,...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - When compound C, which is often used to model a...Ch. 15 - Open the molecular model file for benzyne and...Ch. 15 - The structure of thyroxine, a thyroid hormone that...Ch. 15 - Prob. 2LGPCh. 15 - 3. Deduce the structures of compounds E–L in the...
Additional Science Textbook Solutions
Find more solutions based on key concepts
42. Two of the emission wavelengths in the hydrogen emission spectrum are 656 nm and 486 nm. One of these is du...
Introductory Chemistry (6th Edition)
Balance the following equations by inspection. a. P2H2PH2+P4 b. P4+CI2PCI2 c. FeCI2+H2SFe2S3+HCI d. Mg2N2+H2OMg...
General Chemistry: Principles and Modern Applications (11th Edition)
2. Why shouldn’t you work in a laboratory by yourself?
The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
a. Find potassium (K) in the periodic table and predict how many valence electrons it has. b. What orbital does...
Essential Organic Chemistry (3rd Edition)
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- When trichloroacetaldehyde is dissolved in water, almost all of it is converted to the hydrate. Chloral hydrate, the product of the reaction, is a sedative that can be lethal. A cocktail laced with it is known—in detective novels,at least—as a “Mickey Finn.” Explain why an aqueous solution of trichloroacetaldehyde is almost all hydrate.arrow_forwardWhich is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenolarrow_forwardWhen trichloroacetaldehyde is dissolved in water, almost all of it is converted to the hydrate. Chloral hydrate, the product of the reaction, is a sedative that can be lethal. A cocktail laced with it is known—in detective novels, at least—as a “Mickey Finn.” Explain why an aqueous solution of trichloroacetaldehyde is almost all hydrate.arrow_forward
- The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Of these three anticonvulsants, one is considerably more acidic than the other two. Which is the most acidic compound? Estimate its pKa and account for its acidity. How does its acidity compare with that of phenol? with that of acetic acid?arrow_forward(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enalarrow_forwardIn an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?arrow_forward
- Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. (1) (2) (3) OH (4) 2-ethoxy-1-butanol (racemic) OH Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: OH (c) ethylene oxide (a) (CH3)3CO¯K+, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 Br OH + (9) H₂ SO4 (anhydrous) Na, NH3 (1) (k) NBS, heat (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate) PBr3 (PCC) (h) NaOH (N-bromosuccinimide) Previous Nextarrow_forwardThe (R)-isomer of a-terpineol is a component of perfumes and flavorings and has a lilac-like floral odor. The (S)-isomer has a pine-like odor. Propose two methods of producing a-terpineol using Grignard reactions. [Ignore stereochemistry in your synthesises.]arrow_forwardJj.128.arrow_forward
- (b) State the reagents needed to convert benzoic acid into the following compounds. (i) C6H§COCI (ii) C,H$CH2OH (iii) C6H$CONHCH3arrow_forwardExplain the trends in the acidity of phenol and the monofluoro derivatives of phenol. OH он он он F pк, 10.0 pK, 8.81 pK, 9.28 pK, 9.81arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) 1 Ph THF A Ph Ph B H₂SO4 100 °C 3 OH What is the name of the reaction that is followed by reaction Method A?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY